92855-64-6

Usage

Uses

Used in Organic Synthesis:
6-Benzyloxyindole-3-carboxaldehyde is used as a key intermediate for the synthesis of various bioactive compounds due to its unique structure and reactivity. It plays a crucial role in the development of new organic compounds with potential applications in different fields.
Used in Drug Development:
6-Benzyloxyindole-3-carboxaldehyde is utilized as a building block in the creation of pharmaceuticals, leveraging its versatile reactivity to form new drug candidates with potential therapeutic effects. Its incorporation into drug molecules can lead to the discovery of novel treatments for various diseases and conditions.
Used in Agrochemicals:
6-Benzyloxyindole-3-carboxaldehyde is employed as a precursor in the synthesis of agrochemicals, contributing to the development of new pesticides, herbicides, and other agricultural chemicals. Its unique properties allow for the creation of more effective and targeted agrochemicals to improve crop protection and yield.

InChI:InChI=1/C16H13NO2/c18-10-13-9-17-16-8-14(6-7-15(13)16)19-11-12-4-2-1-3-5-12/h1-10,17H,11H2

Upstream product

• 15903-94-3 6-benzyloxy-1H-indole 
• 68-12-2 N,N-dimethyl-formamide 
• 10025-87-3 trichlorophosphate 

Downstream Products

• 108977-96-4 6-benzyloxy-3-(2-nitro-vinyl)-indole 
• 141834-88-0 N-methyl-N-phenethyl-2-[(6-benzyloxy-3-formyl)indol-1-yl]acetamide 
• 630110-71-3 6-benzyloxy-1H-1-tert-butoxycarbonylindole-3-carbaldehyde 
• 1415333-49-1 (E)-methyl 3-(6-(benzyloxy)-1H-indole-3-yl)acrylate 
• 130288-24-3 (+)-duocarmycin SA 

Relevant academic research and scientific papers

Iodine-Mediated Tryptathionine Formation Facilitates the Synthesis of Amanitins

Synthetic methods on the macrocyclization of peptides are of high interest since they facilitate the synthesis of various types of potentially bioactive compounds, e.g. addressing targets like protein-protein-interactions. Herein, we report on an efficient method to construct tryptathionine-cross-links in peptides between the amino acids Trp and Cys. This reaction not only is the basis for the total synthesis of the death cap toxin α-amanitin but also provides rapid access to various new amanitin analogues. This study for the first time presents a systematic compilation of structure-activity relations (SAR) of amatoxins with regard to RNA polymerase II inhibition and cytotoxicity with one amanitin derivative of superior RNAP II inhibition. The present approach paves the way for the synthesis of structurally diverse amatoxins as future payloads for antibody-toxin conjugates in cancer therapy.

SYNTHESIS OF (S)-6-HYDROXYTRYPTOPHAN AND DERIVATIVES THEREOF

The present invention relates to novel methods and compounds for synthesizing amanitin derivatives. The invention in particular relates to methods for synthesizing (S)-6-hydroxy-tryptophan derivatives which can be used as building blocks for synthesizing

An Enantioselective Total Synthesis of (+)-Duocarmycin SA

An efficient, concise enantioselective total synthesis of the potent antitumor antibiotic (+)-duocarmycin SA is described. The invented route is based on a disconnection strategy that was devised to facilitate rapid and efficient synthesis of key core compounds to enable preclinical structure-activity relationship investigations. The key tricycle core was constructed with a highly enantioselective indole hydrogenation to set the stereocenter and a subsequent hitherto unexplored vicarious, nucleophilic-substitution/cyclization sequence to effectively forge a final indole ring. Additionally, the development of a stable sulfonamide protecting group capable of mild chemoselective cleavage greatly enhanced sequence yield and throughput. An understanding of key reaction parameters ensured a robust, reproducible sequence easily executable on decagram scales to this highly promising class of compounds.

ENANTIOSELECTIVE SYNTHESIS OF PYRROLOINDOLE COMPOUNDS

Compounds according to formula (I) or (II), wherein R1, R2, and R3 are as defined in the specification, are versatile intermediates for the synthesis of DNA minor groove binder- alkylators having a cyclopropapyrroloindole (CPI) or seco-CPI alkylating subunit.

Synthesis of indolyl-3-acetonitrile derivatives and their inhibitory effects on nitric oxide and PGE2 productions in LPS-induced RAW 264.7 cells

Arvelexin is one of major constituents of Brassica rapa that exerts anti-inflammatory activities. Several indolyl-3-acetonitrile derivatives were synthesized as arvelexin analogs and evaluated for their abilities to inhibit NO and PGE2 productions in LPS-induced RAW 264.7 cells. Of the indolyl-3-acetonitriles synthesized, compound 2k, which possesses a hydroxyl group at C-7 position of the indole ring and an N-methyl substituent, more potently inhibited NO and PGE2 productions and was less cytotoxic than arvelexin on macrophage cells.

INDOLE, INDOLINE DERIVATIVES, COMPOSITIONS COMPRISING THEM AND USES THEREOF

The invention provides indole and indoline derivatives and slats thereof, compositions comprising them and uses thereof for the treatment of diseases and disorders.

Carbamate derivatives of indolines as cholinesterase inhibitors and antioxidants for the treatment of Alzheimer's disease

The cascade of events that occurs in Alzheimer's disease involving oxidative stress and the reduction in cholinergic transmission can be better addressed by multifunctional drugs than cholinesterase inhibitors alone. For this purpose, we prepared a large number of derivatives of indoline-3-propionic acids and esters. They showed scavenging activity against different radicals in solution and significant protection against cytotoxicity in cardiomyocytes and primary cultures of neuronal cells exposed to H2O2 species and serum deprivation at concentrations ranging from 1 nM to 10 μM depending on the compound. For most of the indoline-3-propionic acid derivatives, introduction of N-methyl-N-ethyl or N-methyl-N-(4-methoxyphenyl) carbamate moieties at positions 4, 6, or 7 conferred both acetyl (AChE) and butyryl (BuChE) cholinesterase inhibitory activities at similar concentrations to those that showed antioxidant activity. The most potent AChE inhibitors were 120 (3-(2-aminoethyl) indolin-4-yl ethyl(methyl)carbamate dihydrochloride) and 94 (3-(3-methoxy-3-oxopropyl)-4-(((4-methoxyphenyl)(methyl) carbamoyl)oxy)indolin- 1-ium hydrochloride) with IC50s of 0.4 and 1.2 μM, respectively.

Fused [d]pyridazin-7-ones

The present invention is directed to fused [d]pyridazin-7-ones. The invention is also directed to methods for making and using the fused [d]pyridazin-7-ones. In particular, the compounds of the present invention may be effective in the treatment of diseases or disease states related to the activity of VEGFR2, MLK1 and CDK5 enzymes, including, for example, angiogenic disorders and neurodegenerative diseases.

An efficient synthetic route to homocarbonyltopsentine

Efficient synthesis of homocarbonyltopsentine Ia, starting from readily available triiodoimidazole 9 and 3-formylindoles 2 and 18 is described. The key steps of the synthesis are selective halogen-metal exchanges at the imidazole nucleus and subsequent ad